Real Estate Investment Properties for Sale in Winnetka, IL
Looking for investment property in Winnetka, IL with high ROI ?
Explore a variety of short-term homes & houses in Winnetka, IL. Invest wisely with VRBO & Winnetka, IL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Winnetka, IL
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
1333 Tower RoadWINNETKA, ILStep into a beautifully transformed Hemphill home in Winnetka with private access to the F... |
5 beds | 6 baths | 3,921 sq.ft. |
$1,850,000 |
Airbnb cash on cash: N/A
|
1159 Chatfield RoadWINNETKA, ILBlending timeless elegance with modern sophistication, this stunning 2016 Winnetka home fe... |
4 beds | 5 baths | 4,390 sq.ft. |
$2,245,000 |
Airbnb cash on cash: -0.97%
|
1185 Hill RoadWINNETKA, ILIdyllic Cape Cod offering resort-like living with 4+ bedrooms and 5.2 baths, beautifully d... |
4 beds | 7 baths | 4,269 sq.ft. |
$2,439,000 |
Airbnb cash on cash: -0.82%
|
334 Woodland AvenueWINNETKA, IL
|
4 beds | 5 baths | 3,748 sq.ft. |
$2,799,000 |
Airbnb cash on cash: -0.95%
|
916 Oak StreetWINNETKA, ILAn inviting front porch welcomes you into this beautifully renovated home in the heart of ... |
4 beds | 3 baths | 2,116 sq.ft. |
$1,399,000 |
Airbnb cash on cash: 0.13%
|
985 Pine Tree LaneWINNETKA, ILSet on a half-acre, this custom-built 5+ bedroom, 5.1 bath home offers elegant design, wel... |
5 beds | 6 baths | 7,200 sq.ft. |
$2,885,000 |
Airbnb cash on cash: N/A
|
640 Winnetka Mews unit: 405WINNETKA, ILWelcome to this spacious and sun-filled top-floor residence at the Winnetka Mews, a though... |
3 beds | 3 baths | 1,862 sq.ft. |
$639,000 |
Airbnb cash on cash: -2.38%
|
Real Estate investment in Winnetka, IL
There are 9 properties for sale in the city of Winnetka . The median list price in Winnetka is $1,850,000 and the average price per square foot is $454. In March 2026, the average monthly cash on cash return in Winnetka is N/A%. The average monthly rental income in Winnetka is $5,191.